Dave Whelan is recalling the 1960 FA Cup final and the day he suffered the broken leg that ended his top-flight playing career at the age of 23. It is a sunny afternoon and a dark tale he has revisited countless times in the past 53 years but, on this occasion, as he replays the memory to stress the FA Cup's lasting importance, the hardened businessman with the forthright views dissolves from view. The face grows redder, the voice falters, and he begins to cry.

"Sorry. Sorry about that," says the Wigan Athletic chairman as he regains composure and the club's press officer hurries over with a glass of water and a tissue. Talk of Wembley triggered the most unexpected turn in the interview, reducing the 76-year-old to tears and a table of journalists to silence in the Chairman's Suite at the DW Stadium. Wigan can take Whelan back by overcoming Everton in Saturday's quarter-final. He has returned several times since being injured while playing for Blackburn Rovers against Wolverhampton Wanderers; for play-offs, England internationals and in his former role as the owner of Wigan Warriors rugby league club. This would mean so much more.

"To say it would be exciting would be to underestimate every single thing," states Whelan. "It would be extraordinary. I don't know whether anybody has played at Wembley in the FA Cup final and then got there as chairman of a club and led the team out."

The septuagenarian's history with the FA Cup is not rose-tinted. Whelan was in his fourth year as a Rovers defender when, in the 42nd minute of the 1960 final, he committed to a challenge that would alter the course of his life. "There was a ball placed between Norman Deeley and myself," he recalls. "We both went for the ball. I got the ball and he got me, but I'm not saying it was deliberate because accidents happen when you're both fighting like hell for the ball. He did come over the top, there's no question about that. I've still got two stud marks in my leg. But I don't think it was deliberate.

"After that I was carried off on a stretcher. There were no injections, no painkillers then. Luckily the doctor from Wembley hospital, who was Polish, had been watching the match and knew I'd broken my leg. He drove straight to the hospital because he knew I'd be coming in. I was in severe pain, I really was. When they carried me out of the ambulance he was waiting outside with an injection that he stuck straight into my leg and killed the pain in one minute. He set the leg and when I came to it was about half past five and I was being pushed up a corridor in the hospital. I woke and said… it makes me cry now… how have we gone on? He said you've lost three-nil. And I burst into tears. I still feel it."

The tears return at this point. "It's horrendous when you do have an accident like that," Whelan says through them. Deeley, despite also being hurt in the collision, scored twice as Wolves won the Cup while Whelan joined the victims of "The Wembley Hoodoo", so-called after a succession of finals in the 1950s were marred by serious injury – Roy Dwight's broken leg in 1959, a broken cheekbone and brief state of unconsciousness for Ray Wood in 1957, Bert Trautmann's broken neck in 1956 and a broken leg for Jimmy Meadows in 1955. No wonder Nat Lofthouse's charge on Harry Gregg in 1958 was viewed as tame by comparison.

Whelan theorises: "At that time of the season we were used to playing on pitches that were worn, wet and had no grass on them right down the middle. When you walked on to Wembley, the feel, the bounce, the grass, everything about it was totally different to the ground you'd been playing on. It doesn't surprise me you got a few injuries because the players were not used to playing on turf as rich as that. Things did change after I broke my leg because we had three finals absolutely ruined by 10 men playing 11 for more than half the game. The FA introduced one substitute."

Wigan have not advanced this far in the FA Cup since Whelan bought the club in 1995. Recent prospects have not been helped by Roberto Martínez blooding youngsters in the competition and he has vowed to make changes at Goodison Park in search of a winning formula for the Premier League. The priorities of the Wigan manager, and the values of his chairman, appear impossible to reconcile.

Whelan admits: "Sometimes you do think: 'He's not taking the FA Cup seriously enough here,' but we are in a fight to stay in the Premier League. It is nothing new to Roberto. But Roberto does regard the FA Cup very highly, he has played in it himself, and he knows what it means to the English game. I don't know what team he will play at Everton, I never ask and I never put pressure on. But sometimes it is disappointing when teams put out a complete second team and get knocked out. Then you have to wonder if that manager or that football club realises how special the FA Cup is."

SaturSaturday's quarter-final is a rarity by Premier League standards – a contest between two clubs owned by local boys done good. For a traditionalist like Whelan, an FA Cup afternoon with his beloved Wigan and in the company of Bill Kenwright is cause to end a four-week stay in Barbados.

"It is disappointing when you go into a club, like Liverpool last season, and there is not a soul in the boardroom," says the Wigan chairman.

"Eventually two or three lads came in, including the one who works for the BBC, Alan Hansen, to represent Liverpool and you think: 'Where has the heart and soul gone out of this football club?' There are so many foreign owners that the heart and soul has gone out of quite a few clubs. You go to Everton and see Bill and the rest of the people there who are Everton through and through, just as we are Wigan through and through. It's not very often you get that feeling before and after a match anymore."

Whelan never played in the top flight again following his Wembley exit. He spent over two years trying to recapture fitness at Blackburn, in vain, before transferring to Crewe in the old first division. From there, he left to expand the supermarket chain that would make his first million. The injury did, however, result in another, happier memory.

"As the opening match to every season Blackburn used to play Preston in a practice game," Whelan explains. "I was put back in for this match at Deepdale and who should I be playing against but Tom Finney. My first match back after two and a half years and I've got probably the finest right-winger there has ever been. And Tom Finney is the perfect gentleman. He never took me on at all. I took the ball off him three times in the first half and when we were coming off I went to him and said: 'Tom, you're not taking me on.'

"I'd played against him before and I knew how good he was, a phenomenal footballer. He said: 'You've had some bad luck son, and I'm not going to take you on, I want you to get through today's game and get back into the first team.' I'll never forget him saying that to me. He was and still is a total gentleman."